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4-Toluenesulfonyl chloride → HCID 71496931, Verbindung

HRID 1695304
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695304
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=[C:15]([CH2:21][OH:22])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[K+].[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>ClCCl.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][O:20][S:25]([C:28]2[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[N:16]=[C:15]([CH2:21][O:22][S:25]([C:28]2[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=2)(=[O:26])=[O:23])[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 57570973HCID 57570973, Verbindung

Produkt 1

HCID 71496931HCID 71496931, VerbindungAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a precooled (0° C.) solution of 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(hydroxymethyl)-pyridine (76 mg) in dichloromethane (0.7 mL), was added a solution of potassium hydroxide (30 mg) in water (0.3 mL). Tosyl chloride (93.7 mg) was added, and the resulting heterogenous mixture was shaken vigorously for 1 h and then washed into separatory funnel using dichloromethane and water. The layers were separated, and the aqueous layer was extracted three times with dichloromethane. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Interchrom Puriflash 10 g column, SiOH 15-35 μm), using gradient elution with a mixture of heptane (A) and ethyl acetate (B) (gradient: 90% A:10% B up to 50% A:50% B) to give 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(tosyloxymethyl)pyridine (56 mg):

Aufarbeitung

  1. washwashed into separatory funnel
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic solutions were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a residue
  6. customThe residue was purified by silica gel chromatography (Interchrom Puriflash 10 g column, SiOH 15-35 μm)
  7. washelution
  8. additionwith a mixture of heptane (A) and ethyl acetate (B) (gradient

Quellen und Nachweise

ORD-Eintrag
ord-60b2451be580459fb661576ec20010ac
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163736B2

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